The present invention relates to 2-(3-alkenylbenzoyl)cyclohexane-1,3-diones of the formula I 
where the variables have the following meanings:
R1, R2 are hydrogen, nitro, halogen, cyano, thiocyanato, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, xe2x80x94OR6, xe2x80x94OCOR7, xe2x80x94OSO2R7, xe2x80x94SH, xe2x80x94S(O)nR8, xe2x80x94SO2OR6, xe2x80x94SO2NR6R9, xe2x80x94NR9SO2R7 or xe2x80x94NR9COR7;
R3 is hydrogen, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl;
R4, R5 are hydrogen, nitro, halogen, cyano, thiocyanato, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C4-C6-cycloalkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-haloalkoxy, xe2x80x94COR10, xe2x80x94CO2R10, xe2x80x94COSR10, xe2x80x94CONR10R11, xe2x80x94C(R12)xe2x95x90NR13, xe2x80x94PO(OR10)(OR11), C1-C4-alkyl which has attached to it a radical from amongst the following group: hydroxyl, xe2x80x94COR10, xe2x80x94CO2R10, xe2x80x94COSR10, xe2x80x94CONR10R11 or xe2x80x94C(R12)xe2x95x90NR13; heterocyclyl, heterocyclyl-C1-C4-alkyl, phenyl, phenyl-C1-C4-alkyl, hetaryl, hetaryl-C1-C4-alkyl, it being possible for the six last-mentioned radicals to be substituted; or
R4 and R5 together form a C2-C6-alkanediyl chain which can be mono- to tetrasubstituted by C1-C4-alkyl and/or can be interrupted by oxygen or sulfur or by a nitrogen which is unsubstituted or substituted by C1-C4-alkyl;
n is 0, 1 or 2;
R6 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C2-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl;
R7 is C1-C6-alkyl or C1-C6-haloalkyl;
R8 is C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C2-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl;
R9 is hydrogen or C1-C6-alkyl;
R10 is hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, phenyl or benzyl, it being possible for the two last-mentioned radicals to be partially or fully halogenated and/or to have attached to them one to three radicals from amongst the following group: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl;
R11 is hydrogen, C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl; or
R10 and R11 together form a C2-C6-alkanediyl chain which can be mono- to tetrasubstituted by C1-C4-alkyl and/or can be interrupted by oxygen or sulfur or by a nitrogen which is unsubstituted or substituted by C1-C4-alkyl;
R12 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkoxycarbonyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, phenyl or benzyl, it being possible for the two last-mentioned radicals to be partially or fully halogenated and/or to have attached to them one to three radicals from amongst the following group: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, Cl-C4-haloalkoxy, C1-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl;
R13 is C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3xe2x80x94C6-alkynyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-cycloalkyloxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, phenyl, benzyl or phenyl-C1-C4-alkoxy, it being possible for the three last-mentioned radicals to be partially or fully halogenated and/or to have attached to them one to three radicals from amongst the following group:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl;
Q is an unsubstituted or substituted cyclohexane-1,3-dione ring which is linked in the 2-position;
and to agriculturally useful salts thereof.
The invention furthermore relates to processes for the preparation of compounds of the formula I, to compositions comprising them, and to the use of the compounds of the formula I and to compositions comprising them for controlling harmful plants.
WO 93/24446 discloses cyclohexane-1,3-diones which are substituted in the 2-position and which have anthelminthic and nematicidal properties. 2-Benzoylcyclohexane-1,3-diones are also known from the literature, for example from EP-A 135 191, EP-A 137 963 and EP-A 319 075. However, the herbicidal properties of these compounds and their crop plant tolerance are only moderately satisfactory.
It is an object of the present invention to find, in particular, herbicidally active compounds which have improved properties.
We have found that this object is achieved by the 2-(3-alkenylbenzoyl)cyclohexane-1,3-diones of the formula I and their herbicidal action.
We have furthermore found highly active herbicidal compositions which comprise the compounds I. In addition, we have found processes for the preparation of these compositions and methods of controlling undesired vegetation using the compounds I.
The present invention also relates to stereoisomers of the compounds of the formula I. This embraces not only pure stereoisomers, but also mixtures of these.
The compounds of the formula I contain a carbon-carbon double bond and are therefore present in the form of E isomers or Z isomers or E/Z; isomer mixtures. Furthermore, the compounds of the formula I can contain other carbon-carbon or carbon-nitrogen double bonds. The invention relates not only to the pure geometric isomers, but also to mixtures of these.
Equally, the compounds of the formula I can have one or more chiral centers, depending on the substitution pattern, in which case they exist as enantiomer or diastereomer mixtures. The invention relates not only to the pure enantiomers or diastereomers, but also to mixtures of these.
The compounds of the formula I can also exist in the form of their agriculturally useful salts, the type of salt generally being of no importance. In general, the salts of those cations or the acid addition salts of those acids are suitable whose cations, or anions, do not adversely affect the herbicidal action of the compounds I.
Cations which are suitable are, in particular, ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium and magnesium, and of the transition metals, preferably manganese, copper, zink and iron, and also ammonium, it being possible in this case, if desired, for one to four hydrogen atoms to be replaced by C1-C4-alkyl, hydroxy-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkyl, hydroxy-C1-C4-alkoxy-C1-C4-alkyl, phenyl or benzyl, preferably ammonium, dimethylammonium, diisopropylammonium, tetramethylammonium, tetrabutylammonium, 2-(2-hydroxyeth-1-oxy)eth-1-ylammonium, di-(2-hydroxyeth-1-yl)ammonium, trimethylbenzylammonium furthermore phosphonium ions, sulfonium ions, preferably tri(C1-C4-alkyl)sulfonium and sulfoxonium ions, preferably tri(C1-C4-alkyl)sulfoxonium.
Anions of useful acid addition salts are mainly chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of C1-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate.
Mention must be made of the compounds of the formula I according to the invention where the variable Q is a cyclohexane-1,3-dione ring of the formula II 
which is linked in the 2-position, II also representing the tautomeric formulae IIxe2x80x2 and IIxe2x80x3
where
R14, R15, R17 and R19 are hydrogen or C1-C4-alkyl;
R16 is hydrogen, C1-C4-alkyl, C1-C4-haloalkyl or C3-C4-cycloalkyl, it being possible for the three last-mentioned groups to have attached to them one to three of the following substituents: C1-C4-alkylthio or C1-C4-alkoxy; or
is tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, tetrahydrothiopyran-2-yl, tetrahydrothiopyran-3-yl, tetrahydrothiopyran-4-yl, 1,3-dioxolan-2-yl, 1,3-dioxan-2-yl, 1,3-oxathiolan-2-yl, 1,3-oxathian-2-yl, 1,3-dithiolan-2-yl or 1,3-dithian-2-yl, it being possible for the 6 last-mentioned radicals to be substituted by one to three C1-C4-alkyl radicals;
R18 is hydrogen, C1-C4-alkyl or C1-C6-alkoxycarbonyl; or
R16 and R19 together form a xcfx80 bond or a three- to six-membered carbocyclic ring; or
the CR16R17 unit may be replaced by Cxe2x95x90O.
The organic moieties mentioned for the substituents R1-R19 or as radicals on phenyl, hetaryl and heterocyclyl rings represent collective terms for individual enumerations of the individual group members. All hydrocarbon chains, ie. all alkyl, haloalkyl, cycloalkyl, alkoxyalkyl, alkoxy, haloalkoxy, cycloalkoxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, alkenyl, cycloalkenyl, alkynyl, alkenyloxy, alkynyloxy moieties can be straight-chain or branched. Unless otherwise specified, halogenated substituents preferably have attached to them one to five identical or different halogen atoms. Halogen means in each case fluorine, chlorine, bromine or iodine.
Examples of other meanings are:
C2-C4-alkyl: ethyl, n-propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl;
C1-C4-alkyl and the alkyl moieties of C1-C4-alkoxy-C1-C4-alkyl, hydroxy-C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylcarbonyl, heterocyclyl-C1-C4-alkyl, phenyl-C1-C4-alkyl, hetaryl-C1-C4-alkyl: C2-C4-alkyl as mentioned above, and also methyl;
C2-C6-alkyl and the alkyl moieties of C1-C6-alkoxy-C2-C6-alkyl: C2-C4-alkyl as mentioned above, and also pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1-ethyl-1-methylpropyl or 1-ethyl-3-methylpropyl;
C1-C6-alkyl and the alkyl moieties of C1-C6-alkoxy-C1-C6-alkyl: C2-C6-alkyl as mentioned above, and also methyl;
C1-C4-haloalkyl: a C1-C4-alkyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, eg. chloromethyl, dichlorornethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluororopyl, heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl;
C1-C6-haloalkyl: C1-C4-haloalkyl as mentioned above, and also 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl or dodecafluorohexyl;
C1-C4-alkoxy and the alkoxy moieties of C1-C4-alkoxy-C1-C4-alkyl, hydroxy-C1-C4-alkoxy-C1-C4-alkyl and C1-C4-alkoxycarbonyl: methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy;
C1-C6-alkoxy and the alkoxy moieties of C1-C6-alkoxy-C1-C6-alkyl and C1-C6-alkoxycarbonyl: C1-C4-alkoxy as mentioned above, and also pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy;
C1-C4-haloalkoxy: a C1-C4-alkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, eg. fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2,3-dichloropropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy, 1-(fluoromethyl)-2-fluoroethoxy, 1-(chloromethyl)-2-chloroethoxy, 1-(bromomethyl)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy;
C1-C6-haloalkoxy: C1-C4-haloalkoxy as mentioned above and, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy;
C3-C6-cycloalkoxy: cyclopropoxy, cyclobutoxy, cyclopentoxy or cyclohexoxy;
C1-C4-alkylthio: methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio or 1,1-dimethylethylthio;
C1-C6-alkylthio: C1-C4-alkylthio as mentioned above and, for example, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthic, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio or 1-ethyl-2-methylpropylthio;
C3-C6-alkenyl: prop-1-en-1-yl, prop-2-en-1-yl, 1-methylethenyl, buten-1-yl, buten-2-yl, buten-3-yl, 1-methylprop-1-en-1-yl, 2-methylprop-1-en-1-yl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, penten-1-yl, penten-2-yl, penten-3-yl, penten-4-yl, 1-methylbut-1-en-1-yl, 2-methylbut-1-en-1-yl, 3-methylbut-1-en-1-yl, 1-methylbut-2-en-1-yl, 2-methylbut-2-en-1-yl, 3-methylbut-2-en-1-yl, 1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl, 3-methylbut-3-en-1-yl, 1,1-dimethylprop-2-en-1-yl, 1,2-dimethylprop-1-en-1-yl, 1,2-dimethylprop-2-en-1-yl, 1-ethylprop-1-en-2-yl, 1-ethylprop-2-en-1-yl, hex-1-en-1-yl, hex-2-en-1-yl, hex-3-en-1-yl, hex-4-en-1-yl, hex-5-en-1-yl, 1-methylpent-1-en-1-yl, 2-methylpent-1-en-1-yl, 3-methylpent-1-en-1-yl, 4-methylpent-1-en-1-yl, 1-methylpent-2-en-1-yl, 2-methylpent-2-en-1-yl, 3-methylpent-2-en-1-yl, 4-methylpent-2-en-1-yl, 1-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl, 3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl, 1-methylpent-4-en-1-yl, 2-methylpent-4-en-1-yl, 3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl, 1,1-dimethylbut-2-en-1-yl, 1,1-dimethylbut-3-en-1-yl, 1,2-dimethylbut-1-en-1-yl, 1,2-dimethylbut-2-en-1-yl, 1,2-dimethylbut-3-en-1-yl, 1,3-dimethylbut-1-en-1-yl, 1,3-dimethylbut-2-en-1-yl, 1,3-dimethylbut-3-en-1-yl, 2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-1-en-1-yl, 2,3-dimethylbut-2-en-1-yl, 2,3-dimethylbut-3-en-1-yl, 3,3-dimethylbut-1-en-1-yl, 3,3-dimethylbut-2-en-1-yl, 1-ethylbut-1-en-1-yl, 1-ethylbut-2-en-1-yl, 1-ethylbut-3-en-1-yl, 2-ethylbut-1-en-1-yl, 2-ethylbut-2-en-1-yl, 2-ethylbut-3-en-1-yl, 1,1,2-trimethylprop-2-en-1-yl, 1-ethyl-1-methylprop-2-en-1-yl, 1-ethyl-2-methylprop-1-en-1-yl or 1-ethyl-2-methylprop-2-en-1-yl;
C2-C6-alkenyl: C3-C6-alkenyl as mentioned above, and also ethenyl;
C3-C6-alkynyl: prop-1-yn-1-yl, prop-2-yn-1-yl, but-1-yn-1-yl, but-1-yn-3-yl, but-1-yn-4-yl but-2-yn-1-yl, pent-1-yn-1-yl, pent-1-yn-3-yl, pent-1-yn-4-yl, pent-1-yn-5-yl, pent-2-yn-1-yl, pent-2-yn-4-yl, pent-2-yn-5-yl, 3-methylbut-1-yn-3-yl, 3-methylbut-1-yn-4-yl, hex-1-yn-1-yl, hex-1-yn-3-yl, hex-1-yn-4-yl, hex-1-yn-5-yl, hex-1-yn-6-yl, hex-2-yn-1-yl, hex-2-yn-4-yl, hex-2-yn-5-yl, hex-2-yn-6-yl, hex-3-yn-1-yl, hex-3-yn-2-yl, 3-methylpent-1-yn-1-yl, 3-methylpent-1-yn-3-yl, 3-methylpent-1-yn-4-yl, 3-methylpent-1-yn-5-yl, 4-methylpent-1-yn-1-yl, 4-methylpent-2-yn-4-yl or 4-methylpent-2-yn-5-yl;
C2-C6-alkynyl: C3-C6-alkynyl as mentioned above, and also ethynyl:
C3-C4-cycloalkyl: cyclopropyl or cyclobutyl;
C3-C6-cycloalkyl: C3-C4-cycloalkyl as mentioned above, and also cyclopentyl or cyclohexyl;
C3-C6-alkenyloxy: for example prop-1-en-1-yloxy, prop-2-en-1-yloxy, 1-methylethenyloxy, buten-1-yloxy, buten-2-yloxy, buten-3-yloxy, 1-methylprop-1-en-1-yloxy, 2-methylprop-1-en-1-yloxy, 1-methylprop-2-en-1-yloxy, 2-methylprop-2-en-1-yloxy, penten-1-yloxy, penten-2-yloxy, penten-3-yloxy, penten-4-yloxy, 1-methylbut-1-en-1-yloxy, 2-methylbut-1-en-1-yloxy, 3-methylbut-1-en-1-yloxy, 1-methylbut-2-en-1-yloxy, 2-methylbut-2-en-1-yloxy, 3-methylbut-2-en-1-yloxy, 1-methylbut-3-en-1-yloxy, 2-methylbut-3-en-1-yloxy, 3-methylbut-3-en-1-yloxy, 1,1-dimethylprop-2-en-1-yloxy, 1,2-dimethylprop-1-en-1-yloxy, 1,2-dimethylprop-2-en-1-yloxy, 1-ethylprop-1-en-2-yloxy, 1-ethylprop-2-en-1-yloxy, hex-1-en-1-yloxy, hex-2-en-1-yloxy, hex-3-en-1-yloxy, hex-4-en-1-yloxy, hex-5-en-1-yloxy, 1-methylpent-1-en-1-yloxy, 2-methylpent-1-en-1-yloxy, 3-methylpent-1-en-1-yloxy, 4-methylpent-1-en-1-yloxy, 1-methylpent-2-en-1-yloxy, 2-methylpent-2-en-1-yloxy, 3-methylpent-2-en-1-yloxy, 4-methylpent-2-en-1-yloxy, 1-methylpent-3-en-1-yloxy, 2-methylpent-3-en-1-yloxy, 3-methylpent-3-en-1-yloxy, 4-methylpent-3-en-1-yloxy, 1-methylpent-4-en-1-yloxy, 2-methylpent-4-en-1-yloxy, 3-methylpent-4-en-1-yloxy, 4-methylpent-4-en-1-yloxy, 1,1-dimethylbut-2-en-1-yloxy, 1,1-dimethylbut-3-en-1-yloxy, 1,2-dimethylbut-1-en-1-yloxy, 1,2-dimethylbut-2-en-1-yloxy, 1,2-dimethylbut-3-en-1-yloxy, 1,3-dimethylbut-1-en-1-yloxy, 1,3-dimethylbut-2-en-1-yloxy, 1,3-dimethylbut-3-en-1-yloxy, 2,2-dimethylbut-3-en-1-yloxy, 2,3-dimethylbut-1-en-1-yloxy, 2,3-dimethylbut-2-en-1-yloxy, 2,3-dimethylbut-3-en-1-yloxy, 3,3-dimethylbut-1-en-1-yloxy, 3,3-dimethylbut-2-en-1-yloxy, 1-ethylbut-1-en-1-yloxy, 1-ethylbut-2-en-1-yloxy, 1-ethylbut-3-en-1-yloxy, 2-ethylbut-1-en-1-yloxy, 2-ethylbut-2-en-1-yloxy, 2-ethylbut-3-en-1-yloxy, 1,1,2-trimethylprop-2-en-1-yloxy, 1-ethyl-1-methylprop-2-en-1-yloxy, 1-ethyl-1-methylprop-2-en-1-yloxy or 1-ethyl-2-methylprop-2-en-1-yloxy;
C3-C6-alkynyloxy: for example prop-1-yn-1-yloxy, prop-2-yn-1-yloxy, but-1-yn-1-yloxy, but-1-yn-3-yloxy, but-1-yn-4-yloxy, but-2-yn-1-yloxy, pent-1-yn-1-yloxy, pent-1-yn-3-yloxy, pent-1-yn-4-yloxy, pent-1-yn-5-yloxy, pent-2-yn-1-yloxy, pent-2-yn-4-yloxy, pent-2-yn-5-yloxy, 3-methylbut-1-yn-3-yloxy, 3-methylbut-1-yn-4-yloxy, hex-1-yn-1-yloxy, hex-1-yn-3-yloxy, hex-1-yn-4-yloxy, hex-1-yn-5-yloxy, hex-1-yn-6-yloxy, hex-2-yn-1-yloxy, hex-2-yn-4-yloxy, hex-2-yn-5-yloxy, hex-2-yn-6-yloxy, hex-3-yn-1-yloxy, hex-3-yn-2-yloxy, 3-methylpent-1-yn-1-yloxy, 3-methylpent-1-yn-3-yloxy, 3-methylpent-1-yn-4-yloxy, 3-methylpent-1-yn-5-yloxy, 4-methylpent-1-yn-1-yloxy, 4-methylpent-2-yn-4-yloxy or 4-methylpent-2-yn-5-yloxy;
C4-C6-cycloalkenyl: cyclobuten-1-yl, cyclobuten-3-yl, cyclopenten-1-yl, cyclopenten-3-yl, cyclohexen-1-yl, cyclohexen-3-yl or cyclohexen-4-yl;
heterocyclyl and the heterocyclyl radicals in heterocyclyloxy and heterocyclyl-C1-C4-alkyl: three- to seven-membered saturated or partially unsaturated mono- or polycyclic heterocycles which contain one to three hetero atoms selected from a group consisting of oxygen, nitrogen and sulfur, such as oxiranyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofuran-2-yl, 2,3-dihydrofuran-3-yl, 2,3-dihydrofuran-4-yl, 2,3-dihydrofuran-5-yl, 2,5-dihydrofuran-2-yl, 2,5-dihydrofuran-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,3-dihydrothien-4-yl, 2,3-dihydrothien-5-yl, 2,5-dihydrothien-2-yl, 2,5-dihydrothien-3-yl, 2,3-dihydropyrrol-2-yl, 2,3-dihydropyrrol-3-yl, 2,3-dihydropyrrol-4-yl, 2,3-dihydropyrrol-5-yl, 2,5-dihydropyrrol-2-yl, 2,5-dihydropyrrol-3-yl, 2,3-dihydroisoxazol-3-yl, 2,3-dihydroisoxazol-4-yl, 2,3-dihydroisoxazol-5-yl, 4,5-dihydroisoxazol-3-yl, 4,5-dihydroisoxazol-4-yl, 4,5-dihydroisoxazol-5-yl, 2,5-dihydroisoxazol-3-yl, 2,5-dihydroisoxazol-4-yl, 2,5-dihydroisoxazol-5-yl, 2,3-dihydroisothiazol-3-yl, 2,3-dihydroisothiazol-4-yl, 2,3-dihydroisothiazol-5-yl, 4,5-dihydroisothiazol-3-yl, 4,5-dihydroisothiazol-4-yl, 4,5-dihydroisothiazol-5-yl, 2,5-dihydroisothiazol-3-yl, 2,5-dihydroisothiazol-4-yl, 2,5-dihydroisothiazol-5-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,5-dihydropyrazol-3-yl, 2,5-dihydropyrazol-4-yl, 2,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 4,5-dihydrooxazol-2-yl, 4,5-dihydrooxazol-4-yl, 4,5-dihydrooxazol-5-yl, 2,5-dihydrooxazol-2-yl, 2,5-dihydrooxazol-4-yl, 2,5-dihydrooxazol-5-yl, 2,3-dihydrothiazol-2-yl, 2,3-dihydrothiazol-4-yl, 2,3-dihydrothiazol-5-yl, 4,5-dihydrothiazol-2-yl, 4,5-dihydrothiazol-4-yl, 4,5-dihydrothiazol-5-yl, 2,5-dihydrothiazol-2-yl, 2,5-dihydrothiazol-4-yl, 2,5-dihydrothiazol-5-yl, 2,3-dihydroimidazol-2-yl, 2,3-dihydroimidazol-4-yl, 2,3-dihydroimidazol-5-yl, 4,5-dihydroimidazol-2-yl, 4,5-dihydroimidazol-4-yl, 4,5-dihydroimidazol-5-yl, 2,5-dihydroimidazol-2-yl, 2,5-dihydroimidazol-4-yl, 2,5-dihydroimidazol-5-yl, 2-morpholinyl, 3-morpholinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 3-tetrahydropyridazinyl, 4-tetrahydropyridazinyl, 2-tetrahydropyrimidinyl, 4-tetrahydropyrimidinyl, 5-tetrahydropyrimidinyl, 2-tetrahydropyrazinyl, 1,3,5-tetrahydrotriazin-2-yl, 1,2,4-tetrahydrotriazin-3-yl, 1,3-dihydrooxazin-2-yl, 2-tetrahydropyranyl, 3-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothiopyranyl, 3-tetrahydrothiopyranyl, 4-tetrahydrothiopyranyl, 1,3-dioxolan-2-yl, 1,3-dioxolan-4-yl, 1,3-dithiolan-2-yl, 1,3-dithiolan-4-yl, 1,3-dioxan-2-yl, 1,3-dioxan-4-yl, 1,3-dioxan-5-yl, 1,3-dithian-2-yl, 1,3-dithian-4-yl, 1,3-dithian-5-yl, 3,4,5,6-tetrahydropyridin-2-yl, 4H-1,3-thiazin-2-yl, 4H-3,1-benzothiazin-2-yl, 1,1-dioxo-2,3,4,5-tetrahydrothien-2-yl, 2H-1,4-benzothiazin-3-yl, 2H-1,4-benzoxazin-3-yl or 1,3-dihydrooxazin-2-yl;
hetaryl and the hetaryl radicals in hetaryloxy and hetaryl-C1-C4-alkyl: aromatic mono- or polycyclic radicals which, in addition to carbon ring members, can additionally comprise one to four nitrogen atoms or one to three nitrogen atoms and one oxygen or one sulfur atom or one oxygen or one sulfur atom, eg. 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl, 1,3,4-triazol-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl or 1,2,4,5-tetrazin-3-yl, and the corresponding benzo-fused derivatives;
C2-C6-alkanediyl: for example ethane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl or hexane-1,6-diyl.
All phenyl and hetaryl rings are preferably unsubstituted or have attached to them one to three halogen atoms and/or one or two radicals from amongst the following group: nitro, cyano, methyl, trifluoromethyl, methoxy, trifluoromethoxy or methoxycarbonyl.
With a view to the use of the compounds of the formula I according to the invention as herbicides, the variables preferably have the following meanings, in each case alone or in combination:
R1 is nitro, halogen, cyano, thiocyanato, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, xe2x80x94OR6 or xe2x80x94S(O)nR8; especially preferably nitro, halogen, eg. fluorine, chlorine or bromine, C1-C6-haloalkyl, xe2x80x94OR6 or xe2x80x94SO2R8;
R2 is hydrogen, nitro, halogen, cyano, thiocyanato, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, xe2x80x94OR6 or xe2x80x94S(O)nR8; especially preferably hydrogen, nitro, halogen, eg. fluorine, chlorine or bromine, C1-C6-alkyl, C1-C6-haloalkyl, xe2x80x94OR6 or xe2x80x94SO2R8; particularly preferably nitro, halogen, eg. fluorine, chlorine or bromine, C1-C6-alkyl, eg. methyl or ethyl, C1-C6-haloalkyl, eg. difluoromethyl or trifluoromethyl, xe2x80x94OR6 or xe2x80x94SO2R8;
R3 is hydrogen, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl or C2-C6-alkynyl; especially preferably hydrogen, halogen, eg. fluorine, chlorine or bromine, C1-C4-alkyl, eg. methyl or ethyl, C1-C4-haloalkyl, eg. trifluoromethyl, C1-C4-alkoxy, eg. methoxy or ethoxy, allyl or propargyl; particularly preferably hydrogen or methyl;
R4 is hydrogen, nitro, halogen, cyano, thiocyanato, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C4-C6-cycloalkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-haloalkoxy, xe2x80x94COR10, xe2x80x94CO2R10, xe2x80x94COSR10, xe2x80x94CONR10R11, xe2x80x94C(R12)xe2x95x90NR13, xe2x80x94PO(OR10)(OR11), C1-C4-alkyl which has attached to it a radical from amongst the following group: xe2x80x94COR10, xe2x80x94CO2R10, xe2x80x94COSR10, xe2x80x94CONR10R11 or xe2x80x94C(R12)xe2x95x90NR13; heterocyclyl, heterocyclyl-C1-C4-alkyl, phenyl, phenyl-C1-C4-alkyl, hetaryl, hetaryl-C1-C4-alkyl, it being possible for the six last-mentioned radicals, in turn, to be substituted by one to three halogen atoms and/or one to three radicals from amongst the following group:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl;
R5 is hydrogen, nitro, halogen, cyano, thiocyanato, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C4-C6-cycloalkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-haloalkoxy, xe2x80x94COR10, xe2x80x94CO2R10, xe2x80x94COSR10, xe2x80x94CONR10R11, xe2x80x94C(R12)xe2x95x90NR13, xe2x80x94PO(OR10)(OR11), C1-C4-alkyl which has attached to it a radical from amongst the following group: xe2x80x94COR10, xe2x80x94CO2R10, xe2x80x94COSR10, xe2x80x94CONR10R11 or xe2x80x94C(R12)xe2x95x90NR13; heterocyclyl, heterocyclyl-C1-C4-alkyl, phenyl, phenyl-C1-C4-alkyl, hetaryl, hetaryl-C1-C4-alkyl, it being possible for the six last-mentioned radicals, in turn, to be substituted by one to three halogen atoms and/or one to three radicals from amongst the following group: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl;
especially preferably hydrogen, halogen, cyano, thiocyanato, C1-C6-alkyl, C1-C6-haloalkyl, xe2x80x94COR10, xe2x80x94CO2R10, xe2x80x94COSR10, xe2x80x94CONR10R11 or xe2x80x94PO(OR10) (OR11); or
R4 and R5 together form a C2xe2x80x94C6-alkanediyl chain which can be mono- to tetrasubstituted by C1-C4-alkyl and/or can be interrupted by oxygen or sulfur or by a nitrogen which is unsubstituted or substituted by C1-C4-alkyl, for example butane-1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl, 3-oxapentane-1,5-diyl or 3-methyl-3-azapentane-1,5-diyl;
n is 0 or 2
R6 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C2-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl; especially preferably C1-C4-alkyl, eg. methyl or ethyl, C1-C4-haloalkyl, eg. trifluoromethyl or difluoromethyl, C1-C4-alkoxy-C1-C4-alkyl, eg. methoxyethyl, allyl or propargyl;
R8 is C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C2-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl; especially preferably C1-C4-alkyl, eg. methyl or ethyl, C1-C4-haloalkyl, eg. trifluoromethyl, difluoromethyl, C1-C4-alkoxy-C1-C4-alkyl, eg. methoxyethyl, allyl or propargyl;
R10 is hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, phenyl or benzyl; especially preferably hydrogen, C1-C4-alkyl, eg. methyl or ethyl, C1-C4-haloalkyl, eg. trifluoromethyl, allyl, propargyl and benzyl;
R11 is hydrogen, C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl; or
R10 and R11 together form a C2-C6-alkanediyl chain which can be mono- to tetrasubstituted by C1-C4-alkyl;
R12 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkoxycarbonyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, phenyl or benzyl; especially preferably hydrogen, C1-C4-alkyl, eg. methyl or ethyl, C1-C4-alkoxycarbonyl, eg. methoxycarbonyl or ethoxycarbonyl, C1-C4-haloalkyl, eg. trifluoromethyl, or C1-C4-alkoxy, eg. methoxy or ethoxy;
R13 is C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-cycloalkyloxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, phenyl, benzyl, or benzyloxy; especially preferably C1-C4-alkyl, eg. methyl or ethyl, C1-C4-alkoxy, eg. methoxy or ethoxy, allyloxy, propargyloxy, benzyl or benzyloxy;
R14, R15, R17, R19 are hydrogen or C1-C4-alkyl; especially preferably hydrogen, methyl or ethyl;
R16 is hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, C3-C4-cycloalkyl, it optionally being possible for the three last-mentioned groups to have attached to them one to three of the following substituents: C1-C4-alkoxy or C1-C4-alkylthio; tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, tetrahydrothiopyran-2-yl, tetrahydrothiopyran-3-yl, tetrahydrothiopyran-4-yl, 1,3-dioxolan-2-yl, 1,3-dioxan-2-yl, 1,3-oxathiolan-2-yl, 1,3-oxathian-2-yl, 1,3-dithian-2-yl or 1,3-dithiolan-2-yl, it being possible for each of the six last-mentioned groups to have attached to them one to three C1-C4-alkyl radicals; especially preferably hydrogen, methyl, ethyl, cyclopropyl, di(methoxy)methyl, di(ethoxy)methyl, 2-ethylthiopropyl, tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, tetrahydrothiopyran-2-yl, tetrahydrothiopyran-3-yl, tetrahydrothiopyran-4-yl, 1,3-dioxolan-2-yl, 1,3-dioxan-2-yl, 5,5-dimethyl-1,3-dioxan-2-yl, 1,3-oxathiolan-2-yl, 1,3-oxathian-2-yl, 1,3-dithiolan-2-yl, 5,5-dimethyl-1,3-dithian-2-yl or 1-methylthiocyclopropyl;
R18 is hydrogen, C1-C4-alkyl or C1-C4-alkoxycarbonyl;
especially preferably hydrogen, methyl or methoxycarbonyl; particularly preferably hydrogen or methyl.
Equally, it may advantageously be suitable for R16 and R19 to form a xcfx80 bond, so that a double-bond system results.
The CR16R17 unit may advantageously also be replaced by Cxe2x95x90O.
Extraordinarily preferred compounds of the formula I are those where
R1 is nitro, halogen, cyano, thiocyanato, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, xe2x80x94OR6 or xe2x80x94S(O)nR8;
R2 is hydrogen or a radical mentioned under R1, as above.
Especially extraordinarily preferred are compounds of the formula I where
R1 is nitro, halogen, eg. fluorine, chlorine or bromine, C1-C6-haloalkyl, OR6 or SO2R8;
R2 is nitro, halogen, eg. fluorine, chlorine or bromine, C1-C6-alkyl, eg. methyl or ethyl, C1-C6-haloalkyl, OR6 or SO2R8, eg. methylsulfonyl or ethylsulfonyl.
Equally extraordinarily preferred compounds of the formula I are those where
R4 [lacuna] hydrogen, nitro, halogen, cyano, thiocyanato, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-cycloalkyl, C2-C6-alkenyl, C4-C6-cycloalkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-haloalkoxy, xe2x80x94COR10, xe2x80x94CO2R10, xe2x80x94COSR10, xe2x80x94CONR10R11, xe2x80x94C(R12)xe2x95x90NR13, xe2x80x94PO(OR10)(OR11), C1-C4-alkyl which has attached to it a radical from amongst the following group: xe2x80x94COR10, xe2x80x94CO2R10, xe2x80x94COSR10, xe2x80x94CONR10R11 or xe2x80x94C(Rl2)xe2x95x90NR13; heterocyclyl, heterocyclyl-C1-C4-alkyl, phenyl, phenyl-C1-C4-alkyl, hetaryl, hetaryl-C1-C4-alkyl, it being possible for the six last-mentioned radicals to be substituted;
R5 [lacuna] hydrogen, halogen, cyano, thiocyanato, C1-C6-alkyl, C1-C6-haloalkyl, xe2x80x94COR10, xe2x80x94CO2R10, xe2x80x94COSR10, xe2x80x94CONR10R11 or xe2x80x94PO(OR10)(OR11); or
R4 and R5 together form a C2-C6-alkanediyl chain which can be mono- to tetrasubstituted by C1-C4-alkyl and/or can be interrupted by oxygen or sulfur or a nitrogen which is unsubstituted or substituted by C1-C4-alkyl.
Equally extraordinarily preferred are those compounds of the formula I where
R16 is hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, C3-C4-cycloalkyl, it being possible for the three last-mentioned substituents to have attached to them two or three of the following substituents: C1-C4-alkylthio or C1-C4-alkoxy.
Equally extraordinarily preferred compounds of the formula I are those where
R4 is nitro, halogen, cyano, thiocyanato, C1-C6-haloalkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C4-C6-cycloalkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-haloalkoxy, xe2x80x94COR10, xe2x80x94CO2R10, xe2x80x94COSR10, xe2x80x94CONR10R11, xe2x80x94C(R12)xe2x95x90NR13, xe2x80x94PO(OR10)(OR11), C1-C4-alkyl which has attached to it a radical from amongst the following group: xe2x80x94COR10, xe2x80x94CO2R10, xe2x80x94COSR10, xe2x80x94CONR10R11 or xe2x80x94C(R12)xe2x95x90NR13; heterocyclyl, heterocyclyl-C1-C4-alkyl, phenyl, phenyl-C1-C4-alkyl, hetaryl, hetaryl-C1-C4-alkyl, it being possible for the six last-mentioned radicals to be substituted;
R5 is hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, xe2x80x94COR10, xe2x80x94CO2R10, xe2x80x94COSR10, xe2x80x94CONR10R11 or xe2x80x94PO(OR10)(OR11); or
R4 and R5 together form a C2-C6-alkanediyl chain which can be mono- to tetrasubstituted by C1-C4-alkyl and/or can be interrupted by oxygen or sulfur or a nitrogen which is unsubstituted or substituted by C1-C4-alkyl;
Equally especially preferred compounds of the formula I are those where
R1 is nitro, halogen, C1-C6-haloalkyl or C1-C6-alkylsulfonyl; in particular nitro, chlorine, trifluoromethyl, methylsulfonyl or ethylsulfonyl;
R2 is nitro, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-alkylsulfonyl; in particular nitro, chlorine, methyl, trifluoromethyl, methoxy or methylsulfonyl;
R3 is hydrogen or C1-C6-alkyl; in particular hydrogen or methyl; preferably hydrogen;
R4 is hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4-hydroxyalkyl, C1-C4-alkoxy, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl or xe2x80x94C(R12)xe2x95x90NR13; in particular hydrogen, chlorine, bromine, cyano, methyl, ethyl, 2-hydroxyethyl, methoxy, ethoxy, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl or xe2x80x94C(R12)-xe2x95x90NR13;
R5 is hydrogen, halogen, C1-C4-alkyl or C1-C4-alkoxy; in particuclar hydrogen, halogen, methyl, ethyl, methoxy or ethoxy;
R12 is hydrogen, C1-C4-alkyl or C1-C4-alkoxy; in particular hydrogen or methyl;
R13 is C1-C6-alkyl or C1-C6-alkoxy; in particular methoxy or ethoxy;
R14, R15, R16, R17, R18 and R19 are hydrogen or C1-C4-alkyl; in particular hydrogen or methyl;
or the CR16R17 unit can be replaced by Cxe2x95x90O; and where the definitions of radicals R1 to R19 have a particular meaning for the compounds of the formula I according to the invention, not only in combination with each other, but also in each case taken alone.
Especially extraordinarily preferred are compounds of the formula Ia ({circumflex over (=)} I where R1 is bonded in the 4-position of the phenyl ring and R2 is bonded in the 2-position of the phenyl ring). 
Particularly extraordinarily preferred are the compounds Ial ({circumflex over (=)} I where R1xe2x95x90Cl, R14, R15, R16, R17, R18, R19xe2x95x90H, R1 being bonded in the 4-position of the phenyl ring and R2 being bonded in the 2-position of the phenyl ring), in particular the compounds of Table 1, the definitions of the radicals R2 to R5 not only having a special meaning for the compounds according to the invention in combination with each other, but also in each case on their own. 
Equally particularly extraordinarily preferred are the compounds Ia2, in particular the compounds Ia2.001-Ia2.180, which differ from the corresponding compounds Ia1.001-Ia1.180 by the fact that R16 is methyl: 
Equally particularly extraordinarily preferred are the compounds Ia3, in particular the compounds Ia3.001-Ia3.180, which differ from the corresponding compounds Ia1.001-Ia1.180 by the fact that R16 and R17 are in each case methyl: 
Equally particularly extraordinarily preferred are the compounds Ia4, in particular the compounds Ia4.001-Ia4.180, which differ from the corresponding compounds Ia1.001-Ia1.180 by the fact that R18 and R19 are in each case methyl: 
Equally particularly extraordinarily preferred are the compounds Ia5, in particular the compounds Ia5.001-Ia5.180, which differ from the corresponding compounds Ia1.001-Ia1.180 by the fact that the CR16R17 unit is replaced by Cxe2x95x90O: 
Equally particularly extraordinarily preferred are the compounds Ia6, in particular the compounds Ia6.001-Ia6.180, which differ from the corresponding compounds Ia1.001-Ia1.180 by the fact that R14, R18 and R19 are in each case methyl and the CR16R17 unit is replaced by Cxe2x95x90O: 
Equally particularly extraordinarily preferred are the compounds Ia7, in particular the compounds Ia7.001-Ia7.180, which differ from the corresponding compounds Ia1.001-Ia1.180 by the fact that R14, R15, R18 and R19 are in each case methyl and the CR16R17 unit is replaced by Cxe2x95x90O: 
Equally particularly extraordinarily preferred are the compounds Ia8, in particular the compounds Ia8.001-Ia8.180, which differ from the corresponding compounds Ia1.001-Ia1.180 by the fact that R1 is nitro: 
Equally particularly extraordinarily preferred are the compounds Ia9, in particular the compounds Ia9.001-Ia9.180, which differ from the corresponding compounds Ia1.001-Ia1.180 by the fact that R1 is nitro and R16 is methyl: 
Equally particularly extraordinarily preferred are the compounds Ia10, in particular the compounds Ia10.001-Ia10.180, which differ from the corresponding compounds Ia1.001-Ia1.180 by the fact that R1 is nitro and R16 and R17 are in each case methyl: 
Equally particularly extraordinarily preferred are the compounds Ia11, in particular the compounds Ia11.001-Ia11.180, which differ from the corresponding compounds Ia1.001-Ia1.180 by the fact that R1 is nitro and R18 and R19 are in each case methyl: 
Equally particularly extraordinarily preferred are the compounds Ia12, in particular the compounds Ia12.001-Ia12.180, which differ from the corresponding compounds Ia1.001-Ia1.180 by the fact that R1 is nitro and the CR16R17 unit is replaced by Cxe2x95x90O: 
Equally particularly extraordinarily preferred are the compounds Ia13, in particular the compounds Ia13.001-Ia13.180, which differ from the corresponding compounds Ia1.001-Ia1.180 by the fact that R1 is nitro, R14, R18 and R19 are in each case methyl and the CR16R17 unit is replaced by Cxe2x95x90O: 
Equally particularly extraordinarily preferred are the compounds Ia14, in particular the compounds Ia14.001-Ia14.180, which differ from the corresponding compounds Ia1.001-Ia1.180 by the fact that R1 is nitro, R14, R15, R18 and R19 are in each case methyl and the CR16R17 unit is replaced by Cxe2x95x90O: 
Equally particularly extraordinarily preferred are the compounds Ia15, in particular the compounds Ia15.001-Ia15.180, which differ from the corresponding compounds Ia1.001-Ia1.180 by the fact that R1 is methylsulfonyl: 
Equally particularly extraordinarily preferred are the compounds Ia16, in particular the compounds Ia16.001-Ia16.180, which differ from the corresponding compounds Ia1.001-Ia1.180 by the fact that R1 is methylsulfonyl and R16 is methyl: 
Equally particularly extraordinarily preferred are the compounds Ia17, in particular the compounds Ia17.001-Ia17.180, which differ from the corresponding compounds Ia1.001-Ia1.180 by the fact that R1 is methylsulfonyl and R16 and R17 are in each case methyl: 
Equally particularly extraordinarily preferred are the compounds Ia18, in particular the compounds Ia18.001-Ia18.180, which differ from the corresponding compounds Ia1.001-Ia1.180 by the fact that R1 is methylsulfonyl and R18 and R19 are in each case methyl: 
Equally particularly extraordinarily preferred are the compounds Ia19, in particular the compounds Ia19.001-Ia19.180, which differ from the corresponding compounds Ia1.001-Ia1.180 by the fact that R1 is methylsulfonyl and the CR16R17 unit is replaced by Cxe2x95x90O: 
Equally particularly extraordinarily preferred are the compounds Ia20, in particular the compounds Ia20.001-Ia20.180, which differ from the corresponding compounds Ia1.001-Ia1.180 by the fact that R1 is methylsulfonyl, R14, R18 and R19 are in each case methyl and the CR16R17 unit is replaced by Cxe2x95x90O: 
Equally particularly extraordinarily preferred are the compounds Ia21, in particular the compounds Ia21.001-Ia21.180, which differ from the corresponding compounds Ia1.001-Ia1.180 by the fact that R1 is methylsulfonyl, R14, R15, R18 and R19 are in each case methyl and the CR16R17 unit is replaced by Cxe2x95x90O: 
Equally particularly extraordinarily preferred are the compounds Ia22, in particular the compounds Ia22.001-Ia22.180, which differ from the corresponding compounds Ia1.001-Ia1.180 by the fact that R1 is trifluoromethyl: 
Equally particularly extraordinarily preferred are the compounds Ia23, in particular the compounds Ia23.001-Ia23.180, which differ from the corresponding compounds Ia1.001-Ia1.180 by the fact that R1 is trifluoromethyl and R16 is methyl: 
Equally particularly extraordinarily preferred are the compounds Ia24, in particular the compounds Ia24.001-Ia24.180, which differ from the corresponding compounds Ia1.001-Ia1.180 by the fact that R1 is trifluoromethyl and R16 and R17 are in each case methyl: 
Equally particularly extraordinarily preferred are the compounds Ia25, in particular the compounds Ia25.001-Ia25.180, which differ from the corresponding compounds Ia1.001-Ia1.180 by the fact that R1 is trifluoromethyl and R18 and R19 are in each case methyl: 
Equally particularly extraordinarily preferred are the compounds Ia26, in particular the compounds Ia26.001-Ia26.180, which differ from the corresponding compounds Ia1.001-Ia1.180 by the fact that R1 is trif luormethyl and the CR16R17 unit is replaced by Cxe2x95x90O: 
Equally particularly extraordinarily preferred are the compounds Ia27, in particular the compounds Ia27.001-Ia27.180, which differ from the corresponding compounds Ia1.001-Ia1.180 by the fact that R1 is trifluoromethyl, R14, R18 and R19 are in each case methyl and the CR16R17 unit is replaced by Cxe2x95x90O: 
Equally particularly extraordinarily preferred are the compounds Ia28, in particular the compounds Ia28.001-Ia28.180, which differ from the corresponding compounds Ia1.001-Ia1.180 by the fact that R1 is trifluoromethyl, R14, R15, R18 and R19 are in each case methyl and the CR16R17 unit is replaced by Cxe2x95x90O: 
Equally particularly extraordinarily preferred are the compounds I where
R1 is halogen, such as chlorine or bromine, C1-C6-alkylsulfonyl such as mthylsulfonyl or ethylsulfonyl; especially preferably chlorine or methylsulfonyl;
R2 is halogen, such as chlorine or bromine; especially preferably chlorine;
R3 is hydrogen;
R4 is hydrogen, cyano, C1-C6-alkyl such as methyl, ethyl, propyl, 2-methylethyl, butyl or pentyl, C1-C6-alkoxy such as methoxy, ethoxy, C1-C6-alkylthio such as methylthio or ethylthio, formyl, C1-C6-alkylcarbonyl such as methylcarbonyl or ethylcarbonyl, C1-C6-alkoxycarbonyl such as methoxycarbonyl or ethoxycarbonyl, xe2x80x94C(R12)xe2x95x90NR13; heterocyclyl, heterocycl-C1-C4-alkyl, phenyl, hetaryl, it being possible for the four last-mentioned radicals, in turn, to be substituted by one to three halogen atoms and/or two to three radicals selected from amongst the following group: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, in particular C1-C4-alkyl; especially preferably hydrogen, cyano, methyl, 2-methylethyl, pentyl, methoxy, methylthio, formyl, methylcarbonyl, ethoxycarbonyl, xe2x80x94C(R12)xe2x95x90NR13, 2-methyl-1,3-dioxolan-4-yl, 2,2-dimethyl-1,3-dioxolan-4-yl, 1,3-dioxan-2-yl, 1,3-dioxan-2-ylmethyl, phenyl, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl;
R5 is hydrogen, halogen such as chlorine or bromine, or C1-C6-alkoxy such as methoxy or ethoxy; especially preferably hydrogen, chlorine or ethoxy;
R12 is hydrogen, C1-C6-alkyl such as methyl or ethyl, or C1-C6-alkoxycarbonyl such as methoxycarbonyl or ethoxycarbonyl; especially preferably hydrogen, methyl or methoxycarbonyl;
R14, R15, R16, R17, R18 and R19 are hydrogen or C1-C4-alkyl such as methyl or ethyl; especially preferably hydrogen or methyl;
or the CR16R17 unit can be replaced by Cxe2x95x90O.
The 2-(3-alkenylbenzoyl)cyclohexane-1,3-diones of the formula I can be obtained by various routes, for example by the following process:
Reaction of cyclohexanediones of the formula II with an activated carboxylic acid IIIxcex1 or a carboxylic acid IIIxcex2 which is preferably activated in situ, to give the acylation product IV, followed by a rearrangement reaction. 
L is a nucleophilically displaceable leaving group, such as halogen, eg. bromine, chlorine, hetaryl, eg. imidazolyl, pyridyl, carboxylate, eg. acetate, trifluoroacetate, and the like.
The activated carboxylic acid can be employed directly, as in the case of the carboxylic acid halides, or be prepared in situ, for example with dicyclohexylcarbodiimide, triphenylphosphine/azodicarboxylic ester, 2-pyridine disulfide/triphenylphosphine, carbonyldiimidazole and the like.
If appropriate, it may be advantageous to carry out the acylation reaction in the presence of a base. The reactants and the auxiliary base are expediently employed in equimolar amounts. Under certain circumstances, a small excess of the auxiliary base, for example 1.2 to 1.5 mole equivalents, based on II, may be advantageous.
Suitable auxiliary bases are tertiary alkylamines, pyridine or alkali metal carbonates. Examples of solvents which can be used are chlorinated hydrocarbons such as methylene chloride, 1,2-dichloroethane, aromatic hydrocarbons such as toluene, xylene, chlorobenzene, ethers such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran, dioxane, polar aprotic solvents such as acetonitrile, dimethylformamide, dimethyl sulfoxide, or esters such as ethyl acetate, or mixtures of these.
If carboxylic acid halides are employed as activated carboxylic acid component, it may be advantageous to cool the reaction mixture to 0-10xc2x0 C. when adding this reactant. The mixture is subsequently stirred at 20-100xc2x0 C., preferably at 25-50xc2x0 C., until the reaction is complete. Work-up is carried out in the customary manner, for example the reaction mixture is poured into water and the product of value extracted. Solvents which are especially suitable for this purpose are methylene chloride, diethyl ether and ethyl acetate. After the organic phase has been dried and the solvent removed, the crude enol ester of the formula IV is purified, preferably by chromatography. However, it is also possible to employ the crude enol ester of the formula IV in the rearrangement reaction without further purification.
Rearrangement of the enol esters of the formula IV to give the compounds of the formula I is expediently carried out at from 20 to 40xc2x0 C. in a solvent and in the presence of an auxiliary base, with or without the aid of a cyano compound as catalyst.
Examples of solvents which may be used are acetonitrile, methylene chloride, 1,2-dichloroethane, ethyl acetate, toluene, or mixtures of these. The preferred solvent is acetonitrile.
Suitable auxiliary bases are tertiary amines such as triethylamine, pyridine or alkali metal carbonates, such as sodium carbonate or potassium carbonate, which are preferably employed in an equimolar amount or up to a four-fold excess, based on the enol ester. Triethylamine is preferably used, by preference in twice the equimolar ratio based on the enol ester.
Suitable xe2x80x9crearrangement catalystsxe2x80x9d are inorganic cyanides such as sodium cyanide or potassium cyanide and organic cyano compounds such as acetone cyanohydrin or trimethylsilyl cyanide. Normally, they are employed in an amount of from 1 to 50 mol percent based on the enol ester. Substances which are preferably employed are acetone cyanohydrin or trimethylsilyl cyanide, for example in an amount of from 5 to 15, preferably 10, mol percent based on the enol ester.
Work-up can be effected in a manner known per se. For example, the reaction mixture is acidified with dilute mineral acid, eg. 5% strength hydrochloric acid or sulfuric acid, and extracted ith an organic solvent, eg. methylene chloride or ethyl acetate. The organic extract can be extracted with 5-10% strength alkali metal carbonate solution, eg. sodium carbonate or potassium carbonate solution. The aqueous phase is acidified, and the precipitate which forms is filtered off with suction and/or extracted with methylene chloride or ethyl acetate, dried and concentrated.
(Examples of the synthesis of enol esters from cyclohexane-1,3-diones and of the cyanide-catalyzed rearrangement of the enol esters are mentioned for example in EP-A 186 118, U.S. Pat. No. 4 780 127).
The cyclohexane-1,3-diones of the formula II which are used as starting materials and which are not already known can be prepared by processes known per se (eg. EP-A 71 707, EP-A 142 741, EP-A 243 313, U.S. Pat. No. 4 249 937; WO 92/13821).
The activated carboxylic acids IIIxcex1 which are not prepared in situ can be synthesized in a manner known per se. For example, carboxylic acid halides of the formula IIIxcex1 (where L=halogen) can be synthesized by methods similar to those known from the literature (cf. L. G. Fieser, M. Fieser xe2x80x9cReagents for Organic Synthesisxe2x80x9d, Vol. I, pp. 767-769 (1967)) by reacting benzoic acids of the formula IIIxcex2 with halogenating reagents such as thionyl chloride, thionyl bromide, phosgene, diphosgene, triphosgene, oxalyl chloride or oxalyl bromide.
The 3-alkenylbenzoic acids of the formula IIIxcex2 are known from the literature or can be obtained by methods similar to those known from the literature, inter alia by hydrolyzing the corresponding 3-alkenylbenzoic esters (where Mxe2x95x90C1-C6-alkoxy) of the formula IIIxcex3.
The 3-alkenylbenzoic esters (where Mxe2x95x90C1-C6-alkoxy) of the formula IIIxcex3 are also known from the literature or can be obtained by various routes, for example by the following processes: 
The compounds of the formula IIIxcex3 can be obtained by subjecting phosphonium salts of the formula VI to a Wittig reaction with aldehydes or ketones (VII) in a manner known per se (J. March, xe2x80x9cAdvanced Organic Chemistryxe2x80x9d, 3rd ed., p. 864 et seq., Wiley-Interscience Publication, 1985).
The phosphonium salts of the formula VI are accessible from the bromine compounds of the formula V in a manner known per se (J. March, xe2x80x9cAdvanced Organic Chemistryxe2x80x9d, 3rd ed., p. 377 et seq., Wiley-Interscience Publication, 1985). 
The compounds of the formula IIIxcex3 can also be obtained by subjecting aldehydes or ketones of the formula VIII to a Wittig reaction or Horner-Emmons reaction with phosphonium salts IXa (see also A) or phosphonates IXb (J. March, xe2x80x9cAdvanced Organic Chemistryxe2x80x9d, 3rd ed., p. 867 et seq., Wiley-Interscience Publication, 1985).
The compounds of the formula VIII are accessible in a manner known per se by oxidizing bromine compounds of the formula V (J. March, xe2x80x9cAdvanced Organic Chemistryxe2x80x9d, 3rd ed., p. 1105 et seq., Wiley-Interscience Publication, 1985). 
The compounds of the formula IIIxcex3 can also be obtained in a manner known per se by subjecting aldehydes or ketones of the formula VIII to an aldol condensation reaction and related reactions (J. March, xe2x80x9cAdvanced Organic Chemistryxe2x80x9d, 3rd ed., p. 849 et seq., Wiley-Interscience Publication, 1985).